Hello all. I've been lurking here for some time, reading all the threads on buying a new boat. I'm not new to sailing (started with cat boats and Lightnings when I was 12), but I'm new to "big boat" sailing - biggest I've ever really sailed is a J/24. My son is off to the Marine Corps next summer, and I'll have my wife and 2 teenage daughters to go sailing. My wife was receptive-but-reserved until I took her to the Annapolis Boat Show last week, and now she has the bug bad. This is a Good Thing....

The plan is to spend <30K on a weekender in the spring, sail it around the Chesapeake for the next four or five years, then get a used bluewater boat (love the Whitbys) for <100K and move aboard. My employer is very understanding and says they don't care where I work, as long as I have Internet connectivity.

So the immediate problem - which boat to buy next spring? (Isn't that always the way it goes here?)

Requirements: ~30 feet, wheel steering, diesel engine, enclosed head with holding, sound hull, well-maintained rig. Nice to have: lines led aft for singlehanding (this is almost a requirement, but can be done afterwards), propane stove, good electronics, and a dink. I'd like something relatively spritely, for the Thursday night races and good Bay cruising range, but I don't want a Tartan T-10 with pipe berths instead of a comfortable interior.

I plan to keep her on a mooring at a north-Bay marina.

Some of the boats that appeal to my eye, from hours on the for-sale sites, are: S2 9.2A (my favorite so far), Columbia 9.6, Sabre 28, 30' C&C Mk I, 32' Endeavor or Ericson, or the O'Day 322 (which looks sexy, but I don't know if it's a "good" boat). All these boats (along with the Hunters, Catalina 30s, and Bene Firsts) meet the requirements I listed, and some of the nice-to-haves, but I'm not sure where to go to narrow it down, other than to go visit them. I've seen a lot of posts saying, basically, "well, you have a lot of different kinds of boats there," but I'm not sure how to enumerate the differences. Start with PHRF ratings? Go visit them and take notes on what the boats are like? Also, is it better (from a price perspective) to buy in the fall and pay storage, or in the spring after the seller has had it around for the winter?